[(2S,3R,4S,5R,6R)-4-acetyloxy-2-[[(3R,4R,4aR)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-5-hydroxy-6-(hydroxymethyl)oxan-3-yl] 3-hydroxybenzoate

Details

• Internal ID: a73257da-c9f2-4b11-b277-7b072f30dfb1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: [(2S,3R,4S,5R,6R)-4-acetyloxy-2-[[(3R,4R,4aR)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-5-hydroxy-6-(hydroxymethyl)oxan-3-yl] 3-hydroxybenzoate
• SMILES (Canonical): CC(=O)OC1C(C(OC(C1OC(=O)C2=CC(=CC=C2)O)OC3C(C4CCOC(=O)C4=CO3)C=C)CO)O
• SMILES (Isomeric): CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(=O)C2=CC(=CC=C2)O)O[C@@H]3[C@@H]([C@H]4CCOC(=O)C4=CO3)C=C)CO)O
• InChI: InChI=1S/C25H28O12/c1-3-15-16-7-8-32-23(31)17(16)11-33-24(15)37-25-21(36-22(30)13-5-4-6-14(28)9-13)20(34-12(2)27)19(29)18(10-26)35-25/h3-6,9,11,15-16,18-21,24-26,28-29H,1,7-8,10H2,2H3/t15-,16-,18-,19-,20+,21-,24-,25+/m1/s1
• InChI Key: AUBUQPJTUXPAMK-BQQOALTMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₁₂
• Molecular Weight: 520.50 g/mol
• Exact Mass: 520.15807632 g/mol
• Topological Polar Surface Area (TPSA): 167.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 0.55
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8230	82.30%
Caco-2	-	0.8673	86.73%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7636	76.36%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.7922	79.22%
OATP1B3 inhibitior	+	0.9176	91.76%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7131	71.31%
P-glycoprotein inhibitior	+	0.5899	58.99%
P-glycoprotein substrate	-	0.5534	55.34%
CYP3A4 substrate	+	0.6959	69.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8812	88.12%
CYP3A4 inhibition	-	0.8400	84.00%
CYP2C9 inhibition	-	0.7439	74.39%
CYP2C19 inhibition	-	0.7658	76.58%
CYP2D6 inhibition	-	0.8852	88.52%
CYP1A2 inhibition	-	0.7685	76.85%
CYP2C8 inhibition	+	0.7115	71.15%
CYP inhibitory promiscuity	-	0.6447	64.47%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9718	97.18%
Carcinogenicity (trinary)	Non-required	0.5806	58.06%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.9224	92.24%
Skin irritation	-	0.7683	76.83%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6267	62.67%
Hepatotoxicity	-	0.5548	55.48%
skin sensitisation	-	0.7731	77.31%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5470	54.70%
Acute Oral Toxicity (c)	III	0.5947	59.47%
Estrogen receptor binding	+	0.8185	81.85%
Androgen receptor binding	+	0.6659	66.59%
Thyroid receptor binding	-	0.5278	52.78%
Glucocorticoid receptor binding	+	0.6753	67.53%
Aromatase binding	-	0.5640	56.40%
PPAR gamma	+	0.6254	62.54%
Honey bee toxicity	-	0.7643	76.43%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8730	87.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.66%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.76%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.25%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.15%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.67%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.33%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.49%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.95%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.31%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.19%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	88.55%	91.19%
CHEMBL226	P30542	Adenosine A1 receptor	88.43%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	87.89%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.53%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	87.22%	91.49%
CHEMBL220	P22303	Acetylcholinesterase	86.42%	94.45%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.08%	89.67%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.13%	91.24%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.47%	94.80%

Plants that contains it

• Centaurium erythraea

Cross-Links

• PubChem: 163050751
• LOTUS: LTS0265371
• wikiData: Q105100146